Usher Raymond was spotted out and about on the streets of NYC recently with his current boo, Grace Miguel.

The multi-talented singer apparently has a habit of falling for older women and letting them affect his business decisions.

When he chose to marry Tameka Foster Glover Raymond, she put her foot down and fired his entire staff, including his mom/manager Jonetta Patton, who he subsequently rehired after realizing his mistake.

Well now it looks like history is repeating itself for poor Ursh.

Word on the curb is that his current lady love, 43-year-old former Def Jam executive, Grace Miguel has filled Meka’s shoes quite nicely. Grace, who reportedly acts as Usher’s co-manager and stylist, has urged the R&B superstar to cut his entire team and replace them with her people of her choosing!

Usher’s longtime agent, Mark Cheatham of CAA, is the first victim of his much older girlfriend. Usher, 32, started his career with Cheatham and introduced him to teen sensation Justin Bieber, whom he currently represents.

Cheatham was tight-lipped when we contacted him. “I don’t know anything about it. I’ve been with Usher for a long time,” he told us. “I’ve been on great terms with Usher. Talk to my publicist.”

A CAA publicist never got back to us, but Usher is no longer listed on their client list.

A source close to Cheatham tells us, “Mark is really upset. He’s been with him from the beginning. He thinks Usher will come back, He’s just waiting.”

Usher has a history of mixing business with pleasure. In 2007, he married his stylist, Tameka Foster, with whom he has two children. He filed for a divorce in 2009. When Foster was at odds with his mother and manager Jonetta Patton, Usher showed his mom the door.

Usher explained to Vibe: “[I paid her] the ultimate compliment — to retire her to be a full-time grandmother.”

Now it’s Miguel who’s apparently got his ear. A source told us, “Usher will do whatever she wants him do right now.”

Is Grace Miguel ‘Tameka 2.0’?

What is it about Usher and these cougars? He must have some serious mommy issues…

She worked them hips and thighs on his dumb asz and now he’s turned out. That seems to happen to this dude a lot. But, then Kandi says he’s good in bed so she heard. Good enough to get whipped on! Punk! LOL!

NAME WITH HOLD

THE ONLY THING I HAVE TO SAY IS BULL SHIT!!!! GRACE CAN GO TO HELL JUST LIKE USHEREX TAMEKA THEY MAKE A GREAT COUPLE TAMEKA AND GRACE THEY ARE GAY THEY BORTH LOOKED LIKE MEN GRACE IS STILL MARRYED TAMEKA WENT BACK TO HER FRIST HUSBAND THEY NEED TO GO TO HELL AND NEED TO LEAVE USHER THE FUCK OFF AND LET HIM BE HAP-PY WITH HIS FAMILY DAME THOSE HOES MF!!!!!!!!!!!!!!!!

Hot Caddy Girl

This so-called relationship WILL NOT last! Why does Usher keep getting with these older, manly looking women? He can’t do any better than that?!! C’mon Ush….get it together!

I’m telling you Usher and Chilli would solve all their relationship woes if they just got back together cos neither of them have been right since they split what with Usher humping every old woman in sight and Chilli tryna figure out what she wants. What is this now Season 10 and she still ain’t figured out what she wants. hisssssssss

Real

Usher know he don’t want that woman because she is not cute. I don’t want to be rude. Usher and Chilli both are lost without each other. They really need to find love with each other again. The two were the most beautiful couple ever. When they talk about each other, they shines.

rihannajz

He went from one Krazy Kat to the other, LOL how sad remember Usher those Old Red Bones are crazy as _ell also.

ok

Usher Usher Usher!! Why would he go down the same path again!! His career will not uphold this 1!! As soon as he publicly admit to this relationship his career is completely over! The best beat is for him to call it quicks now, she isn’t worth your career USHER..

Some younger men like older women.Wondering why he didn’t stay with Chilli, but after watching her show it seems she wants a "perfect" man. Sorry that title only belong to JESUS.Don’t waste any more time looking.She can’t accept ANY flaws, guess that’s why she ain’t got a man.

Gwendella

Some fools oops I mean ppl never learn.

Kamalla

Why is everybody tripping on Usher dating an older woman? The man is 32 y’all!!! He’s not 17 anymore. He’s a divorced father of two and there has only ever been a 10 year age difference between hims and his girlfriends/wives. He has a mother and that relationship is what it’s supposed to be.

If this is your thinking then I suppose Beyonce got daddy issues since Jay is wayy older than her. Nene Leakes got daddy issues since Gregg is wayy older than her. Ciara had daddy issues since Fiddy was older than her. I could go on and on….